4-Methylphenylhydrazine monohydrochloride → HCID 53904691, compound

HRID 615002Notes

Reaction equation

HRID 615002 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][CH:16]([C:20](=O)[CH3:21])[C:17](=O)[CH3:18])[CH3:12].C([O-])(=O)C.[Na+]>C(O)C>[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]1[C:17]([CH3:18])=[N:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:10])=[CH:3][CH:4]=2)[C:20]=1[CH3:21])[CH3:12]

Participants

5

Reactant 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 517045Sodium Acetate

Product 1

HCID 53904691HCID 53904691, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.0 grams p-tolylhydrazine-hydrochloride, 9.3 grams 3,3-diacetyl-propionic acid-ethyl ester, 4.1 grams anhydrous sodium acetate and 70 milliliters ethanol were mixed and the mixture was heated to the boiling temperature under reflux for 1.5 hour. The reaction mixture was worked up as described in Example (3a). After distillation, 12.1 grams 3,5-dimethyl-1-(p-tolyl)pyrazol-4-acetic acid-ethyl ester were obtained as a viscous oil having a Kp0.001 of 145°-146° C., representing a yield of 89%. For analysis, the product was redistilled resulting in an nD20 1.5455.

Workup

  1. temperaturethe mixture was heated to the boiling temperature
  2. temperatureunder reflux for 1.5 hour
  3. distillationAfter distillation

Sources & evidence

ORD record
ord-42412f33b23d42fab4cabad6176e1bc8
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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